Issue 3, 2023

Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

Abstract

The synthesis of organochalcogen-functionalized chromenones starting from diorganyl dichalcogenides and alkynyl aryl ketones has been developed. Selectfluor® mediates these cyclization/organochalcogenation reaction sequences under mild and open-to-air conditions. The six-membered heterocycles were obtained via a selective 6-endo-dig cyclization compatible with the use of both diorganyl diselenides and disulfides. This synthetic methodology still proved to be versatile to synthesize organochalcogen-substituted thiochromenone and isocromenone derivatives.

Graphical abstract: Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

Supplementary files

Article information

Article type
Paper
Submitted
13 Nov. 2022
Accepted
10 Dec. 2022
First published
12 Dec. 2022

New J. Chem., 2023,47, 1076-1080

Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

T. Anjos, E. L. Gutterres, D. A. Barancelli, R. Cargnelutti, B. Godoi, T. Barcellos and R. F. Schumacher, New J. Chem., 2023, 47, 1076 DOI: 10.1039/D2NJ05567H

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